Tiny house holiday rentals in Dutchess County

Our second time staying at Maitopia with our cat, just as wonderful in a different warmer season. Tina was super responsive as usual and even accommodated a late checkout. We enjoyed feasting in the kitchen as well as grilling in the yard, floating around in the pool when it was warm enough out, "hiking" with our cat on a leash around the forest on the property, taking baths, streaming music. We didn't leave the property much, but it was a fun highlight to get a few local produce items at nearby Greig farm and meet the adorable goats. One tip- bring an eyemask if you're sensitive to light in the mornings- there aren't any window shades in the bedroom.

An incredibly charming, rustic, simple and comfortable small cottage, in a gorgeous rural setting. Just as advertised. It was perfect. Right across the road is Tivoli Bays, with beautiful trails for walking and hiking, and a small waterfall too. If you like, it's just a short walk to Broadway, the main strip in the village of Tivoli. You'll find a few restaurant options, a small market, sandwich shop, excellent coffee, and homemade ice cream. I met Yuko who couldn't be nicer and was a pleasure to chat with. A great experience all around - highly recommend booking a stay!

Had a lovely at Seth’s place, he was very responsive, gave clear instructions and great recommendations. Was the perfect getaway isolated within nature!

Staying in the Ex of In House was an unforgettable experience for my family. The architecture is unlike anything we’ve encountered — both compact and expansive, with light and form constantly shifting as you move through the space. My wife, son, and I found it not only beautiful, but also deeply peaceful. Our son was thrilled to sleep at the top of the sphere, which added a touch of wonder to the stay. It's a house that invites curiosity and reflection. We would absolutely recommend it to anyone interested in design, nature, and the future of living

The location was very quiet and an easy walk into Tivoli. I recommend that the refrigerator is raised by putting a cabinet underneath, or a taller refrigerator. I microwave would be a definite plus.

My friends and I loved our weekend getaway at Vivian's lake house. Vivian was a very responsive host and provided clear instructions that made our stay seamless. The space was super clean, modern, and easily accommodated all 8 of us. The highlight of our trip was spending time on the lake with the provided kayaks and paddle boards. We enjoyed ending the day by grilling and sitting around the fire pit. We wish we had stayed longer!

Magnificent place! Even better hosts!! If ever I need a place to stay when visiting anywhere near, I’m staying here again!! I highly recommend this cottage:))))) They go above and beyond to make your stay as perfect as possible. Thank you, Tommy for being the best!

This was a perfect weekend getaway from Manhattan- we absolutely loved Noa’s arc! It rained most of the weekend (a bit of a bummer) but it was so nice being on the creek and looking out the windows into the beautiful surroundings. When the sun came out, we were able to take advantage of the amazing roof deck, battle putt, and giant (watercolor!) jenga. It was clean, comfortable, and had everything we needed for a nice weekend in Kingston. Not only will we be back, but now we’re considering investing in a houseboat ourselves! Book this place- you won’t be disappointed!

We loved our stay at Olivia’s place and in Rhinebeck. The space was very cozy and well decorated. Their recommendations were great

I needed a place to stay for a night while I had some renovations done in my house. This was such a unique place that we decided to stay here (the little church house). The outdoor surroundings were beautiful and peaceful. The sound of the creek across the road was so relaxing to listen to. Inside was very charming. Everything was clean. Pat and Christine were very helpful and prompt with their responses. I definitely recommend this place. ❤️💯

Good spot to explore Beacon. We walked to Main Street and Día Beacon. Also walked to and from train. The tiny home is great for 1-2 people. Comfortable bed and great shower! Highly recommend.

Incredible hospitality and communication. Place is just as described. Quiet, peaceful location. Comfortable bed and enough space. Beautiful backyard. This is a hidden little gem.

We had a wonderful stay in the treehouse. This place looked exactly like the photos. The room was cozy and the back porch area felt so calm and serene. The outdoor bathtub was the highlight! We would highly recommend booking this place and we hope to return in the future.

The Hobbit House is as wonderful as one might imagine. Certainly the outside is charming and unique, but so too is the inside, filled with magical decorations, swords, maps, and even carved concrete ceilings! And the hot tub was preheated, and the water pressure was adequate, and the mountains and rock formations were awesome, and the bed was comfy, and our 30th anniversary will be a bright spot in our memories forever.

Really comfortable space and serene location. I would totally stay here again when I’m in the Hudson Valley.

Absolutely loved this cozy place ! Felt right at home . So peaceful and relaxing. The host Julie was incredible ,friendly and quick responsive. Needed a break from the city and this location was just perfect! Was able to take a few minutes drive to get food etc . Julie recommended some areas which was helpful because I was new to the area . Definitely recommend this cozy place . Just the right size and peaceful. Love this will be definitely returning! Thanks Julie !

The cabin was exactly as listed and MORE! The nature and privacy you have will make you feel as though you've been transported to a different universe. Paul was an excellent host, providing clear instructions and recommendations, as well as proactively checking in to make sure the stay was going well! 10/10 recommend!!

Rony Island is as cute as it looked online. Perfect lil getaway for us for the weekend. Hosts were so responsive and had lots of recommendations — we had a beautiful dinner at Stissing House and my partner Jon went up to the fire tower for a hike. We spent our last hour at the island slowly paddling the canoe around the whole lake. Thank you for a lovely stay!

I loved this house, so comfortable, clean and attractive. The beds were super comfortable and the shower had good hot water and good pressure. Very pretty and peaceful yard.